


Monopoly

by sinstares (sidestares)



Category: Be More Chill - Iconis/Tracz
Genre: Awkward First Times, Awkward Sexual Situations, Board Games, First Time Blow Jobs, M/M, Michael is jelly of the others, Pining Michael, Post-Squip, Riding, awkward makeouts, boyf riends - Freeform, i hate mself, if u squint, it's really just Jeremy and Michael, its my first time writing idek, meremy hell, s in, sin is in the second chapter ;)), they're so awkward whoops :'), why did I write this
Language: English
Status: Completed
Published: 2018-03-11
Updated: 2018-03-31
Packaged: 2019-03-30 01:59:54
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 4,213
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13940145
Author URL: https://archiveofourown.org/users/sidestares/pseuds/sinstares
Summary: Jeremy promises Michael anything he wants in exchange for Parks Place





	1. Monopoly

**Author's Note:**

> So, this is my first time writing anything on ao3  
> My first time writing smUt (coUGH)  
> I'd say publishing my own fanfiction but I wrote a Soul Eater self-insert when I was like 12
> 
> For some reason in the tags it won't capitalize Brooke's name and I don't know why
> 
> im sorry

To put it in the simplest terms, Michael was bored. Of course, he was used to boredom, especially in school (math, specifically. How many ways could the school force them to solve for “x”?), but this was a different, special kind of boredom. This boredom was specifically known as, _Monopoly_.

“Mikey!” the boy was snapped out of his thoughts and looked up quickly. “Mikey, are you even paying attention?” Jeremy continued, chuckling. Michael felt his face heat up as he looked down at the game board, realizing that it was his turn. Even more embarrassing, however, was that his best friend called him by a nickname in front of _other people_. Namely, Christine, Rich, Jake, Brooke, Chloe, and Jenna. All of Jeremy’s past tormentors, now friends, were sat in a semi-circle next to Michael, all having been invited to Jeremy’s house to “hang out” - it was like a tinier version of the parties Jake would hold, except at Jeremy’s house and without booze.

Michael threw the dice - four spaces. He moved along his tiny metal thimble, landing on “Go To Jail!” He sighed and moved his piece across the board as Chloe picked up the dice.

“Too bad, headphones! Better luck next time.” Michael flinched as he received a slap on the back from Rich, immediately followed by laughter. _They’re just being friendly,_ he was forced to remind himself. _Just a couple more hours of this before they go home - then it’s just me, Jeremy, and_ Apocalypse of the Damned _._ While all the others were to just play games and watch movies, Michael was to stay the night, as the two usually would on weekends such as this. For now, however, he was to quietly observe and wait it out.

As time went on, it became quite obvious that Jeremy was about to win. His face was gone pink from laughing so much, having fun with his friends, Michael noted. _I hope they’re not better friends than me,_ was the next thought. He frowned slightly, continuing to watch Jeremy play. The pale boy had the most valuable piece of property in the game - Boardwalk - as well as several other high-ranking pieces, complete with hotels. Boardwalk didn’t have any hotels, as the colorset was incomplete. The one piece that he needed to secure his victory was currently being mortgaged by Michael, himself only having a meager $20 left.

“Michael,”

“Yessir?” his head perked up, hearing his name on Jeremy’s lips. _Wait - sir? I didn’t mean to-_

“I’m gonna offer you a trade…” Jeremy’s turn. Michael looked down at his little _Monopoly_ belongings, somewhat confused as to what he could possibly trade. He was, however, even more curious.

“I’m listening.”

“I want Parks Place.” Michael’s only property.

“For..?” He leaned forward expectantly, but Jeremy stayed silent, only staring right back. “Jer, don’t tell me-”

“Please, Mikey? I’m so close to winning, ple~~~ase?” Jeremy put his hands together and bowed his head, continuing to whine and beg.

“What? Bro, that’s cheating!” Jake blurted out in protest, everyone smiling and holding back laughter.

“Awe, shut up, it’s a deal, and deals are allowed!” Michael laughed as Jeremy attempted to defend himself.

“Micah, please?” Jeremy turned back to him, and the boy blushed at the use of his pet name. “C’mon, please? I’ll do anything, Mikey, just please give me Parks Place?”

“Oh really?”

“Yes, anything, just please?” Michael chuckled, finally shaking his head and handing Jeremy his card despite the shouts of protest from the others. He smiled at Jeremy, being thanked profusely. Everyone was having fun, including himself.

 

After about half an hour more, Jeremy had wiped everyone out, laughing as he claimed his victory. Eventually, after a little while longer of fun and laughter, they said their final goodbyes as everyone made their leaves, leaving only himself and Michael in his house. While he loved spending time with everyone else, Jeremy was excited to be alone with his favorite person. Having spent so much of his energy with the others, he was more than ready to chill out in his boxers and play games with Michael.

“Hey Micah,” he began, starting to pour some snacks in bowls to bring upstairs to his room. “Ready to play some _Apoc_?” Silence. Jeremy turned around, raising an eyebrow at Michael from his kitchen.

“Michael? Michael!” Finally, the boy seemed to snap back into reality, looking up at Jeremy.

“Oh, uh, sorry, I was just- uh, er- yeah?” His face was completely red as he met Jeremy’s eyes.

“Are… you okay?”

“Oh, yeah, totally!” Michael laughed, rubbing the back of his head. “Just spaced out, is all.” He decided not to press his friend further.

“C’mon, man. Let’s go up.”

Much to Jeremy’s discontent, Michael continued his bizarre behavior even as they were playing. He was constantly dying, stuttering, seemingly distracted. Whenever Jeremy would look back at him, he would find the boy staring directly at him, only to quickly look away and hide his face, fiddling with either his hoodie string, his controller, or the pillow in his lap. Finally, his worry got the best of him as he set down his controller, turned off the gaming console, and turned to Michael. The shorter boy jumped a little bit, surprised to see the screen go black. Michael turned towards Jeremy, his face heated.

“Mikey…” Jeremy sighed, looking Michael in the eye and placing a gentle hand upon his knee. “You’ve been acting really weird today, seriously. Talk to me, man. What’s up?” Then, to his surprise, Michael responded immediately.

“Do you remember that deal we made earlier?”

**Notes for the Chapter:**

> constructive criticisms? yes please ;))


	2. The Good Stuff

**Summary for the Chapter:**

> The boys do the Great Sex.

**Notes for the Chapter:**

> took me a while, i know, but here it is  
> so awkward, oof  
> let me know if you guys want other versions of this, featuring trans michael and/or trans jeremy ;)  
> im sorry

“Th-the one we made in _Monopoly_..?” Jeremy suddenly remembered that he had a side of a deal to uphold - anything Michael wants.

“Yeah! So- so like, I didn’t really think much of it at the time, right?” Jeremy nodded. “But like, since I lost first and I wasn’t really- I wasn’t really talking, so I had time, like, to think, and, like, my- my brain, o-of course, it w-went to- like, the first thing I thought of-”

“Hey, hey, slow down.” Jeremy’s face dusted slightly pink, imagining all of the things that Michael could request that would make him so flustered. “Keep going.”

“The… the first thing I thought of was, like, f-fucking you…” Michael paused, his face with a dark blush. “A-and now I can’t stop thinking about it!”

Michael hid his face in his hands as Jeremy began processing the words, struggling to piece it all together as his heart began to race.

“Y-you want to…” his mind flashed through all of the possibilities. Himself under Michael, moaning in delight, or maybe himself riding Michael, the tan boy sat lazily underneath as he watched Jeremy tire himself out - he realized Michael was talking again, and pressed his legs together in an attempt to hide his growing erection.

“-was just, like, a thought! I mean, of course, I wouldn’t force you to do anything like that! Like, if you actually wanted to, that- that’d be amazing! But, I mean, I don’t want to be, like, taking advantage of you or anything- I mean, I’m pretty sure you’re straight, you had that huge thing for Christine way back,”

“Mikey-”

“-And like, we’re best friends, so that would, like, be super weird, and-”

“Michael, I’m bi!” Jeremy’s face was red, embarrassed. He didn’t think he’d come out like that. _At least it got Michael to stop talking, right?_

“O-oh.. c-congratulations? I mean-” Jeremy let out a small chuckle, and Michael smiled as well. He felt himself relax a bit, anxiety calming down. “How long? How long have you known, I mean?”

“Well, uh..” Jeremy let out a small sigh, leaning against Michael’s shoulder. “A little bit after Christine and I started dating, I guess? It wasn’t really working out, and I realized that… I guess I just didn’t feel the same level of attraction for her as I did to guys? Like, I still liked her, of course, but just... yeah.” He was cool. So cool. The coolest. Jeremy was very okay. So okay. He was great. _This is fine. This is totally fi-_

“For, uh, for your part of the deal, um…” Michael spoke hesitantly, still bothered. Jeremy was no longer totally okay and cool and fine. _Fuck_.

“Y-yeah? I mean, yes?” He sat back up, looking his friend in the eye.

“Could we just, um… could I just, like - fuck - can I kiss you? You can say no, I don’t really care, but..”

“Wh-what? But I thought you said- do you not want to-”

“Jesus Christ, Jeremy, did you think I was going to force you i-into something like that? F-fuck, kissing is already probably too far-” Michael was cut off by the sudden occurrence of lips against his own. He closed his eyes after a moment, surprised at first, then comfortable with the warm sensation coursing through his body. The kiss was sloppy and inexperienced, the taller boy quite obviously having little to no experience. Michael brought a hand to the back of Jeremy’s head, letting him know that he was taking the lead. Jeremy relaxed, allowing Michael to turn their awkward kiss softer and more loving. _Fuck,_ was he a good kisser.

Finally, Michael pulled away. “Woah..” The pillow that was seated in his lap had been knocked to the floor during the event, revealing tented boxers. He, however, was more focused on the boy hovering slightly above him, kneeling, leaning forward with hands on Michael’s knees for support. His face was persimmon, eyes wide as he bit his lip softly. _Fuck,_ was he hot. “J-Jer- woah.”

Jeremy said nothing, only nodding slightly as he kept steady eye contact. He could feel his heart in his throat, his face hot. With all of his willpower, he tried not to focus on his own boner, or let his eyes drift down to Michael’s crotch- _shit,_ he did it, eye-dick contact. His stomach did a flip as he felt a sharp twinge even lower down.

“Jeremy,” God, he had seen Michael in his boxers before - they always take off their jeans while the play video games, to get more comfortable - but this was an entirely different experience. Jeremy wanted them off. In all of the pornos he had seen, the dominant guy would just rip off the other’s boxers when he wanted to fuck. Was he the dominant guy? He’d never really thought about it, besides the thought earlier of him riding Michael-

“Jeremy you’re hurting my legs.” The boy quickly realized that his full weight was still on Michael’s legs, and stumbled back a bit, sat on his own legs. The other boy chuckled softly, getting up and sitting on Jeremy’s bed, which was only a bit away from where the boys were sitting. “I-I swear, Jer, the things you d-do to me. You’re a horrible kisser by the way.”

“H-hey! I- it was just a bad angle is all!” Michael laughed as Jeremy sat on the opposite end of the bed as well.

“Oh yeah? Prove it, then.” What am I saying? Jeremy blushed, biting his lip as Michael laughed. He took a deep breath and stood up on his bed, placing a hand on Michael’s shoulder to steady himself as he lowered onto the boy’s lap, wrapping his legs around his waist and essentially straddling him. “O-oh.”

Jeremy’s cock loved the attention, pressed up against Michael, even through tented fabric. It was even happier, feeling the boy’s own hard-on beneath. Jeremy took a breath and took Michael’s head in his hands, giving a soft, tender kiss. His legs involuntarily tightened as the other kissed back, pulling Jeremy closer and slipping a tongue into his mouth. _Holy shit._ He ground down on Michael to the best of his ability, mind torn between the need for any friction and the dance of tongues. The tan teen moaned softly, breaking the kiss to breathe.

“F-fuck, Jer-bear… I guess I was wrong.” Jeremy only rest his hands on Michael’s shoulder, resting his head in the crook of his neck and whining softly as he continued to grind down on Michael. “A-ah, fuck,” He bit his lip, leaning back a bit. “You’re really fucking horny aren’t you, baby boy?” Jeremy whimpered at the nickname, continuing to nuzzle Michael’s neck.

“Yes, sir…” He replied, barely audible.

“God- g-get up, Jer.” Jeremy did as told, worried that he did something wrong. After watching so many pornos, he had assumed that he knew what to do in sex - was he wrong? It was his first time, but, had Michael fucked any guys? The thought was cold against the back of his neck as he watched Michael take off his hoodie, then shirt, tossing them to the side of Jeremy’s room. _Oh._ “A-are we… uh, is this okay?”

“Y-yes, fuck yes!” Jeremy nodded, heart pounding in anticipation. _God,_ did he look hot. He only imagined how much better his dark skin would look peppered with hickies all along his neck and collarbones.

“Just.. promise me that this isn’t because of the fucking deal, or pity or anything, Jer?” Jeremy stopped his train of thought, looking Michael in the eye. “Y-you’re not just doing this because of any of that, right? I mean, I- I just-”

“I promise, I’m doing this because I want to, and I- I sincerely, genuinely love you, Michael. I promise you.” Jeremy spoke softly, smiling as he saw Michael’s tension dissipate.

“S-sorry if I ruined the mood…” Michael smiled, embarrassed at himself. Why would he distrust Jeremy? He’s known the kid most of his life, for fuck’s sake, he knew that his best friend wasn’t that type of person. “If- c-could you.. Take your boxers off? If we’re doing this, I mean.”

Jeremy nodded and sat up a bit, taking off his shirt and raising his hips off of the bed as he tucked his thumbs underneath the waistband of his boxers. _This is happening,_ he told himself contentedly as he slid off the last piece of his clothing, revealing his boner, already trembling with precome.

“Woah..” Michael gazed in awe at the nude boy in front of him.

“S-stop being weird!” The pale boy looked away, blush creeping past his face and down to his shoulders. “Wh-what are you even gonna do, anyw- _Ah!_ ” He moaned, caught off guard as a warm tongue swiped across the head of his dick, and quickly covered his mouth. He trembled with pleasure, Michael’s hands situated at his thighs, head only inches away from Jeremy’s crotch.

“Huh, fun noise..” Michael was laying on his stomach, moving a hand from Jeremy’s leg and wrapping it around his sizable cock. He gave it a few experimental tugs, and made a mental note that Jeremiah Heere is not quiet in bed. “J-Jesus, Jer, I’m not even doing anything.”

“S-sorr-s- _Ah!_ ” Another load moan sounded through the room, Michael having to move slightly out of the way as hips bucked up towards his face. “Sh-shit, sorry,”

“Jeremy, how am I supposed to suck your fucking dick if you can’t even handle one stroke of my hand?” Jeremy bit his lip, grounding himself a bit. He gave Michael a small look that he hoped gave off the impression of _“Fuck me,”_ and not _“I’m going to come in the next fifteen seconds because just the image of you shirtless and next to my cock is doing that much for me.”_

“Well, d-don’t get upset at me if I’m not good, th-this is my first time.” Huh, him, too- Michael made quick work of using Jeremy’s precome to slick up his cock, then enveloping his soft lips around the top, licking the head once more. Jeremy had to move a hand to his mouth and bite down to keep himself from nearly screaming in pleasure. The tanned boy went deeper, closing his eyes as he tested his limits, also testing how to put his tongue to get the loudest sound out of Jeremy.

Only but a moment after he began moving up and down, using a hand to work what he couldn’t fit in his mouth, a hand was tangled in his hair, pressing him further. Michael gave a small moan around Jeremy as he went even deeper, nose nearly touching the taller boy’s torso. He picked up the pace, Jeremy getting gradually louder. He tried to focus on breathing through his nose, though a bit difficult.

_“A-ahn, M-Michael! F-fuck, close, I’m close!”_ He took this as a good sign and began to attempt to suppress his gag reflex in order to take in Jeremy fully ( _thanks, WikiHow_ ) but the hand in his hair pulled him up and off. He half-opened his eyes, panting and looking up at Jeremy in confusion. “I- is it- is it okay if- if I- _f-fuck,_ Michael, I-”

“Wh-what’s up, Jer?”

“W-would it be cool if I- can- I have some l-lube in my desk drawer, is it- I want to ride you.” Jeremy tried to catch his breath, wiping his brow and looking down at the dark teen beneath him. _Fuck,_ he was so hot. Mouth open, lips ever so slightly swollen, big brown eyes gazing up through half-closed lips, drool running down his chin. The boy wiped his face as he sat up again, leaning against one of the several pillows on Jeremy’s bed.

“Okay, I’m sorry but what?” Michael pushed his hair out of his eyes and gave a look of confusion.

“L-like, it’s just an idea, you can say no, but like, you know… You’d be, like… sitting down or maybe laying down, and-”

“I know what riding is, Jeremy, I’m not fucking twelve - _why the fuck do you have lube in your desk?_ ” He felt his face flush with embarrassment as he looked down - _wait no that’s Michael’s dick_ \- as he looked away, staring at his bedroom door.

“I- I just- they had a sale at _CVS_ -” Michael sighed.

“N-nevermind, I don’t- er- are you sure you wanna do this?” Jeremy nodded. “Alright, w-well, g-go get it, I guess? I’ll t-take off my boxers.” The taller boy found himself staring as he sat up and made his way across the room to his desk, watching Michael shimmy out of his weed boxers ( _nerd_ ) to unveil his erection. _Damn_.

Jeremy sat himself back down on his bed, next to Michael as he struggled to take the little plastic covering off of the lid.

“S-sorry, I just-” After a few grunts of frustration, the little plastic bottle was free. “Fucking nailed it, first try, 360 no-scope one shot one kill-” He was cut off by wild laughter next to him.

“Jer, I swear to God!” Michael leaned back and put a hand over his eyes, the other clutching his stomach as he laughed.

“Sh-shut up! I just- I have short nails is all!” Jeremy felt a certain warmth in his stomach as he popped open the tiny cap, legs trembling slightly. _This is happening. Am I dreaming? I’ve gotta be dreaming. Is this lucid dreaming?_ He looked over at Michael in uncertainty. _Nope, definitely not a dream_.

“S-so… do I just..? Do I just lay down and do nothing?”

“Uh, I think so? I’ve never… I just thought maybe..?” He sighed. “J-just relax, I guess? I’ll, um.. yeah.” Michael took a breath, trying to get comfortable on Jeremy’s bed, act cool and unbothered despite his knowledge of what to come and what had already taken place. Woah.

Suddenly, he felt his back arch and breath get caught in his throat as a chilled substance began to lather itself all around his cock. Jeremy’s hand then began slickly pumping him, causing Michael to moan in delight.

“F-fuck, it’s fucking cold, Jer,”

“Oh, sorry, do you want me to-”

“N- fuck, no, don’t stop.” Michael bit his lip. It was an entirely different experience than just jerking off in his basement, high, there was this certain level of uncertainty added. It was really, _really hot_. He felt several moans bubbling up, only letting himself give out the occasional grunt. _What the fuck do I do with my other hand?_ Alas, the greatest uncertainty of all presented itself before him.

Thankfully, his uncertainty was put to ease as soon as it had arisen. He let out a small grunt of confusion when Jeremy removed his hand, but was pleasantly surprised to see the pale teen sat back, applying lube to his entrance, his toes curling slightly from the cold.

“Sh-shit, Jer. Can you even- are you-” Michael paused, deciding to rather take in the sight before him than question the situation. Then, softly, “A-are you sure you want to do this?”

“D-definitely. And you’re okay with this?”

“Fuck, Jer! I’m more than okay with this!” Michael took Jeremy’s wrist and pulled him in for a sloppy, passionate kiss. He kissed back, not breaking away as he situated himself above Michael and placed hands on his shoulders in order to steady himself. Finally, he took a deep breath, holding on tightly to the darker boy as he lowered himself down.

There was a sharp gasp, followed by a low moan as he eventually settled into Michael’s lap, panting and stopping to situate himself. It was a new experience, and he loved it. Michael stilled himself, heart pounding. _Holy. Shit._ He held Jeremy, pressing soft kisses to his neck.

“Y-you okay?”

“Mm, just.. r-readying myself?”

“T-take your time?” What was Michael supposed to say? He didn’t know how to be sexy! Jeremy nodded slowly, taking a few more deep breaths. Then, without warning, he moved his hips a bit, grinding down on Michael and causing them both to moan. “Wh-what do I do?”

“J-just relax? Let me, uh…” He swiftly brought himself up then back down again, the skin against skin further proving his point. He internally kicked himself for being weak. He was doing everything in his power not to come yet, but he felt himself starting to slip, nearly completely overtaken by feeling. “ _Fuck,_ ah, M-Micah…”

“Uhn?”

“I-I’m… I’m really- I-” Jeremy began fucking himself on Michael again, picking up his speed. “S-so, _ah,_ M-Mikey, I- _ah,_ ”

“G-go- go ahead,” Michael could feel his orgasm creeping closer as well, keeping his hands at Jeremy’s hips. _Fuck,_ was he tight. “C- _fuck,_ come for me, Jer, come for me baby boy, f- _fuck!_ ” Michael’s own moaning cut himself off as Jeremy picked up the pace, bouncing up and down, even sometimes pulling fully off of Michael only to snap all the way back down.

“F- _ah,_ fuck! Michael! M-Micah!” He repeated Michael’s name over and over like a chant as he came, still moving until even the end of his orgasm, literally riding it out. Michael’s fingers were pressed hard down into his hips, likely leaving bruises, as he arched his back and moaned along in complete and total pleasure.

“W-woah, holy shit..” Jeremy panted softly, leaning against Michael. “You okay?” His question was met by a small nod, the boy still coming down from the high of his orgasm. Michael sighed contentedly, giving Jeremy a small kiss.

“Y-you didn’t… you didn’t come.” Jeremy spoke quietly and softly, his breath hot against Michael’s neck. It sent a shiver down his spine.

“That’s okay, man, don’t even worry about it, now c’mon, let’s clean you up-” As Michael began to sit up in order to move Jeremy off of him, a hand tightened against his shoulder. He stopped and leaned back to look the boy in the eyes. “Jer?”

“I- I want to keep going.”

“But-” Jeremy proved his point by grinding down on him, causing Michael to throw his head back in a moan. “ _Fuck!_ ”

“P-please? I w-want you t-to…” Michael was met with pleading eyes, heart racing as Jeremy slowly began to fuck himself out again, looking to him for permission.

“A-are you sure?” Jeremy nodded, causing Michael to sigh. “Jesus, Jer- f-fine, damn it, keep going, _f-fuck,_ you’re so good,” His words faded out, replaced by sounds of pleasure. After his orgasm, Jeremy was extremely sensitive, every movement he made ten times amplified as he overstimmed himself. He let out a small gasp of surprise as Michael tightened his grip on Jeremy’s hips and began to thrust up into him, causing near screams of pleasure from the fucked out boy.

This was enough to send Michael over the edge, arching his back and failing to warn Jeremy as he came, filling the room with echoed moans. Jeremy continued, helping Michael finish before pulling himself off, a panting mess. He laid down next to the shorter boy, draping an arm across the boy’s chest and holding him close.

“Holy shit, Mikey..”

“Mnn..” Michael wrapped an arm around Jeremy, using his free hand to push back his hair. “Yeah… good?”

“Mhm, definitely… w-we should-”

“Yeah, I know,” Michael grumbled lowly. “I’ll clean us up in a sec, just, let me…” He trailed off, somewhat exhausted.

“If you want, I can-”

“I saw the way your legs were shaking, Jeremy, don’t even try to stand up. Just cuddle with me.” Jeremy smiled as Michael turned to his side, also turning Jeremy to spoon him. It was warm, safe, secure.

And the best sex either had ever had.

**Notes for the Chapter:**

> leave some constructive criticisms lovelies, also some suggestions for future stories maybe?


End file.
